3-Amino-2-methylbenzoic acid methyl ester → 3-Hydroxy-2-methylbenzoic Acid

HRID 368342노트

반응식

HRID 368342 반응식
N[C:2]1[C:3]([CH3:12])=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7]C)=[O:6].N([O-])=[O:14].[Na+]>CC(O)=O.OS(O)(=O)=O.O>[OH:14][C:2]1[C:3]([CH3:12])=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([OH:7])=[O:6]

참가 물질

6

반응물 2

HCID 38010253-Amino-2-methylbenzoic acid methyl esterHCID 23668193Sodium Nitrite

생성물 1

HCID 2520233-Hydroxy-2-methylbenzoic Acid수율 94.5%

시약·촉매·용매 3

HCID 176Acetic Acid용매HCID 962Water용매2회HCID 1118Sulfuric Acid용매2회

실험 절차

A solution of 20.6 g (0.125 mol) of methyl 3-amino-2-methylbenzoate in 150 mL of HOAc and 25 mL of conc. H2SO4 was cooled in ice and diazotized by the dropwise addition of a solution of 8.7 g (0.125 mol) of NaNO2 in 50 mL of H2O. After stirring for 15 minutes, the diazonium solution was added dropwise to a boiling solution of 200 mL of 50% H2SO4, and the refluxing continued for 15 minutes after the addition was complete. The mixture was diluted with H2O and extracted twice with Et2O. The Et2O was washed 5 times with H2O, then with saturated NaCl. Drying over MgSO4 and removal of the solvent under reduced pressure left 17.98 g (94.4% yield) of the product as a tan solid, mp 137-140° C. The structure was confirmed by NMR spectroscopy.

후처리

  1. waitthe refluxing continued for 15 minutes
  2. additionafter the addition
  3. extractionextracted twice with Et2O
  4. washThe Et2O was washed 5 times with H2O
  5. dry with materialDrying over MgSO4 and removal of the solvent under reduced pressure

출처 및 근거

ORD 기록
ord-61b4ee59aeeb45a5bcc882f5bfbec47c
출처 데이터셋
uspto-grants-2000_10
특허 번호
US06133303

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